Defensive publication

ABSTRACT

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

DEFENSIVE PUELIEATIQN UNITED STATES PATENT OFFICE Published at therequest of the applicant or owner in accordance with the Notice of Dec.16, 1969, 869 O.G. 687. The abstracts of Defensive Publicationapplications are identified by distinctly numbered series and arearranged chronologically. The heading of each abstract indicates thenumber of pages of specification, including claims and sheets ofdrawings contained in the application as originally filed. The files ofthese applications are available to the publlc for inspection andreproduction may be purchased for 30 cents a sheet.

Defensive Publication applications have not been examined as to themerits of alleged invention. The Patent Ofiice makes no assertion as tothe novelty of the disclosed subject matter;

PUBLISHED AUGUST 8, 1972 T901,017 CATALYTIC HYDROGENATION Fredrick L.Hamb and John F. Stenberg, both of Kodak Park Works, 1669 Lake Ave.,Rochester, N.Y. 14650 Filed Sept. 23, 1970, Ser. No. 74,850

Int. Cl. C07c 69/54 US. Cl. 260-486 R No Drawing. 18 Pages SpecificationCompounds having the structure C Hr-Z wherein is selected from a benzenenucleus and a cyclohexane nucleus;

represents a cyclohexane nucleus and Z is -H or -OH, may be prepared inhigh yields by reducing a dialkyl 1,2,3,4-tetrahydro 2,6naphthalenedicarboxylate in the presence of hydrogen and a hydrogenationcatalyst such as copper chromite. The reaction may be carried out at atemperature of about 100 C. to 350 C., preferably about 140 C. to 220 C.at a pressure of about 500 to 6000 p.s.i., preferably about 1500 to 3500psi.

In another embodiment of the invention, the compounds are prepared in atwo-stage reduction, the first stage comprising reducing dialkyl2,6-naphthalcnedicarboxylate in the presence of hydrogen and a nickelcatalyst, such as Raney nickel to provide high selective yields ofdialkyl 1,2,3,4-teitrahydro-2,6-naphthalenedicarboxylate which issubsequently reduced in a second stage reduction as aforementioned. Thefirst reduction may be carried out at a temperature of about C. to 100C., preferably C. to C. at a pressure of about to 5000 p.s.i.,preferably 1000 to 3000 psi.

Novel monomers may be prepared from the monoalcohols resulting from thereduction of the invention by condensation with acrylic acids and estersthereof such as acrylic acid, methacrylic acid, ethacrylic acid, methylmethacrylate, ethyl methacrylate and ethyl acrylate. Homopolymers orcopolymers of the novel monomers may be prepared by heating the monomersby themselves or with dissimilar polymerizable ethylenically unsaturatedmonomers in the presence of free-radical initiating catalysts such ashydrogen peroxide, benzoyl peroxide, lauroyl peroxide, sodiumpersulfate, potassium persulfate and peracetic acid, for example.

The polymers which can be prepared from the novel monomer compounds ofthe invention in the manner just described can be used to preparephotographic film supports using known techniques.

